INGENOL MEBUTATE

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Trade Names	INGENOL MEBUTATE PICATO
Synonyms	AGN 204332 Ingenol mebutate PEP-005 PEP005 Picato
Status
Molecule Category	UNKNOWN
ATC	D06BX02
UNII	7686S50JAH


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	VDJHFHXMUKFKET-WDUFCVPESA-N
Smiles	C/C=C(/C)C(=O)O[C@H]1C(C)=C[C@]23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@]12O)[C@H]1[C@@H](C[C@H]3C)C1(C)C
InChI	InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C25H34O6
Molecular Weight	430.54
AlogP	2.33
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	3.0
Polar Surface Area	104.06
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	31.0

Assay Description	Organism	Bioactivity	Reference
Activation of PKCdelta (unknown origin) using phosphatidylserine as substrate	Homo sapiens	4.1 nM
Induction of IL-8 release in human primary epidermal keratinocytes after 6 hrs by HTRF assay	Homo sapiens	10.3 nM
Induction of TNFalpha release in human primary epidermal keratinocytes after 6 hrs	Homo sapiens	11.2 nM
Induction of oxidative burst in polymorphonuclear leukocytes (unknown origin) isolated from buffy coat after 40 mins by fluorescence assay	Not specified	8.7 nM
Activation of PKCdelta (unknown origin) after 40 mins	Homo sapiens	4.1 nM
Induction of proimflammatory activity in human primary epidermal keratinocytes assessed as IL-8 release after 6 hrs	Homo sapiens	10.3 nM
Induction of proimflammatory activity in human primary epidermal keratinocytes assessed as TNFalpha release after 6 hrs	Homo sapiens	11.2 nM
Immunostimulatory activity in polymorphonuclear leukocytes (unknown origin) assessed as induction of oxidative burst after 40 mins by fluorescence assay	Not specified	8.7 nM
Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viability after 5 days by MTT assay	Human immunodeficiency virus 1	17.0 nM
Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viability after 5 days by MTT assay	Human immunodeficiency virus type 2 (ISOLATE ROD)	9.0 nM
Activation of PKC in human platelet assessed as induction of platelet aggregation measured within 15 mins by tribidimetric method	Homo sapiens	72.5 nM
Reactivation of latent HIV1 infected in human U1 cells assessed as increase in p24 production after 48 hrs by ELISA	Human immunodeficiency virus 1	4.8 nM
Antiviral activity against Human immunodeficiency virus 1 NL4-3 infected in human MT4 cells measured on day 3 post infection by Nano-Glo luciferase reporter gene assay	Human immunodeficiency virus 1	4.5 nM
Reactivation of latent HIV1 infected in human U1 cells assessed as increase in p24 production after 72 hrs by ELISA	Human immunodeficiency virus 1	4.2 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	1.08 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	10.71 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-0.1615 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	2.17 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	1.7 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	1.7 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	2.17 %

Related Entries

Cross References

Resources	Reference
ChEMBL	CHEMBL1863513
DrugCentral	4226
FDA SRS	7686S50JAH
Guide to Pharmacology	7443
PubChem	6918670
SureChEMBL	SCHEMBL2526605
ZINC	ZINC000100037855

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).